Ethylene Glycol → 2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

HRID 2064963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064963
N#N.[Br:3][C:4]1[N:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1.[CH2:13](O)[CH2:14][OH:15].COC(OC)OC.C([O-])([O-])=O.[Na+].[Na+]>>[Br:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:10]2([CH3:11])[O:15][CH2:14][CH2:13][O:12]2)[N:9]=1

Komponenten

6

Edukt 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 10340Sodium CarbonateHCID 112985782-Acetyl-6-bromopyridine

Produkt 1

HCID 121642822-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(6-bromo-pyridin-2-yl)-ethanone (1880 mg, 9.40 mmol) in ethylene glycol (10.00 mL, 179.32 mmol) was treated with trimethylorthoformate (2.10 mL, 19.16 mmol) followed by LiBF4 (180 mg, 1.88 mmol). The reaction mixture was heated at 95° C. for 5 h. Sat. aq. Na2CO3 was added and the mixture was extracted twice with ether and the combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.57.

Aufarbeitung

  1. extractionthe mixture was extracted twice with ether
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (20:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-19b3232da5d94c09913d23b8c689078d
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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